24 of Carrie Bradshaw's wildest and most questionable outfits on 'Sex and the City'

HBO‘Sex and the City’ costume designer Patricia Field bought Carrie’s iconic tutu skirt for five dollars.
  • Carrie Bradshaw, portrayed by Sarah Jessica Parker, was the resident fashionista on HBO’s hit show “Sex and the City.”
  • She is equally known for her trendy looks as she is for her wacky ones.
  • Here are 24 of her weirdest looks.

If there was one TV character whose legacy is inextricably linked to her clothing, it’s Carrie Bradshaw.

During her six-year run on “Sex and the City,” Sarah Jessica Parker’s on-screen persona was cemented as a style icon and fashion risk-taker, from that timeless tutu in the show’s opening sequence to her $US50,000 karaoke outfit in the second film.

But as any fashionista knows, not every risk pays off – and Carrie is no exception.

Here are 24 of her wackiest, weirdest, and most baffling looks.


When she paired an ’80s prom dress with an Hermès headscarf.

HBOWhy isn’t the scarf folded properly?

Many of Carrie’s stylistic decisions involve questionable headgear, but this placement of a Hermès headscarf is one of her worst. And then, never one for minimalism, Carrie threw in a random boutonniere and an impossibly ruched dress for good measure.


When she wore a newsboy cap and with a two-tone knit romper.

HBOShe accessorized with flowers and a baguette.

Though it initially appears Carrie has donned short shorts and a tube top (underneath a long jacket worthy of “The Matrix”), the centrepiece of this bizarre outfit is actually a knit romper.


When her skirt included an inexplicable tail.

HBOIt almost looks like a bunny tail.

From the front, Carrie’s button-down-and-skirt combo is simple and chic, but when she turns around, some kind of tail is revealed.


When she basically wore a bird on her head to get married.

Warner Bros.Her wedding dress was designed by Vivienne Westwood.

Carrie’s first wedding look was beautiful and elegant. But then she added blue bird feathers as an accessory to the side of her head, for some reason.


When she wore a newspaper as a dress.

HBOShe can often be spotted wearing her ‘Carrie’ necklace.

While this Dior dress – which actually made two separate appearances in the show – is definitely classic Carrie, that doesn’t make it any less strange.


When she wore a bandeau bra to “the event of the season” in the Hamptons.

HBOThe girls attend a billionaire’s yearly hoedown during a trip to the Hamptons.

Considering the event was “a big hoedown full of cowboys and caviar,” in Carrie’s words, her hat is excusable. But why she decided to attend the party in a bandeau bra, long skirt, and rainbow armband is inexplicable.


When she wore this weirdly fancy hat on a casual date.

HBOIt resembles hats worn by British guests to a royal wedding.

In fact, Carrie’s then-boyfriend Jack Berger poked fun at the accessory.


When she wore this unfortunate bucket hat.

HBOUnfortunate headgear is a theme in Carrie’s life.

The outfit also included a white tank top and blue-and-purple blazer.


When she wore a tie over her slinky black dress.

Warner Bros.Carrie wore this to celebrate her wedding anniversary in the second ‘Sex and the City’ film.

The addition of the tie is simply baffling, especially considering she wore this outfit to eat dinner at home.


When she carried an umbrella when it wasn’t raining.

HBOOtherwise, her blue knit dress is quite becoming.

It was a sunny day, and yet Carrie apparently insisted on bringing an umbrella to complete her look.


When she wore knee-high rainbow socks.

HBOShe donned a red slip dress to lounge in her own apartment.

The socks were both loud and unnecessary.


When she layered cargo shorts over her bathing suit.

HBOSamantha helped her friends sneak into the pool at SoHo House.

In another episode, she pairs men’s board shorts with a bikini top.


When she wore a dress that resembles multiple bandanas stitched together.

HBOThere’s so much going on here.

Carrie’s multicolor dress is confusing enough on its own – but she took it to the next level with a cowboy hat and some kind of holey shawl.


When she wore this pinstripe mess.

HBOCarrie is dedicated to her questionable hats.

Only Carrie could pull off this attempt at business casual.


When she couldn’t have possibly worn more pearls.

HBOThis takes layering to new heights.

You can also spot Carrie’s first engagement ring hanging around her neck.


When she wore a belt around her bare waist.

HBOThat belt isn’t serving any purpose.

Even without the belt, this lime-green-and-pale-pink outfit is a lot to take in.


When she paired a Dior t-shirt with a massive skirt.

Warner Bros.Carrie wore this outfit to explore Abu Dhabi.

The individual pieces of this outfit were probably not meant to go together.


When she paired purple sunglasses with a silk headscarf.

HBOShe also went with heavy black eyeliner.

This look would only be acceptable in a ’90s music video.


When she couldn’t get enough of stripes.

HBOCarrie wore this outfit for her first day living in Paris.

This monochromatic look is made even more chaotic by the flat cap on top.


When her shirt looked like it had been shredded.

Warner Bros.Carrie wore this outfit in the first ‘Sex and the City’ movie.

Clothing slits may be trendy, but perhaps not like this.


When it must have been laundry day.

HBOCarrie is wearing nearly every colour of the rainbow.

Not only did Carrie pair tie-dye leggings with a multicolor top, she topped off the look with a blue bandana and questionable earrings.


When she put a cloud around her dress.

HBOThe puffy addition seems inconvenient, at least.

Carrie took the asymmetrical dress trend to the next level.

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